Trifluoroacetic acid → HCID 9855884, compound

HRID 2308218Notes

Reaction equation

HRID 2308218 reaction equation
C[CH2:2][N:3]([CH2:6][CH3:7])[CH2:4]C.[C:8](Br)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:17]#[C:18]N.C(O)(C(F)(F)F)=O.BrC#[N:29]>C(Cl)Cl.CCOC(C)=O>[C:4]([N:3]1[CH2:2][CH:7]([CH2:18][NH:17][C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6]1)#[N:29]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 9864CyanamideHCID 10476Cyanogen BromideHCID 12056Benzoyl bromide

Product 1

HCID 9855884HCID 9855884, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Following general procedure 10, to a stirred solution of the amine (48) (100 mg, 1 equiv.) and Et3N (0.11 mL, 1.5 equiv.) in CH2Cl2 (5 mL) was added benzoyl bromide (0.07 mL, 1.1 equiv.). The resultant mixture was stirred at rt for 10 minutes. The mixture was then diluted with EtOAc and washed successively with 10% citric acid, H2O and brine. The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution: 50% EtOAc in hexane to 70% EtOAc in hexane) to afford the desired coupled product. The N-Boc group of the coupled product was then converted to the cyanamide (N—CN) following general procedure 3 (i.e. successive treatment with TFA and BrCN). The crude material was purified by flash chromatography (gradient elution: 50% EtOAc in hexane to 67% EtOAc in hexane) to afford the desired solid N-[(1-cyano-3-azetidinyl)methyl]benzamide (49).

Workup

  1. washwashed successively with 10% citric acid, H2O and brine
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (gradient elution: 50% EtOAc in hexane to 70% EtOAc in hexane)
  6. customto afford the
  7. customThe crude material was purified by flash chromatography (gradient elution: 50% EtOAc in hexane to 67% EtOAc in hexane)

Sources & evidence

ORD record
ord-3b60b84906b54a6c87422d26ed82930d
Source dataset
uspto-grants-2004_12
Patent number
US06835727B2

Reaction notes

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